31 people have viewed this property this week.

Cayman Castle

5 Bedrooms
5.5 Bathrooms
14 Sleeps

Cayman Castle sits directly oceanfront on a private 2-acre gated estate and enjoys a wide white-sandy beach with fabulous snorkeling, kayaking, and sunbathing.

Two private pools, multi-tiered ocean terraces, a panoramic veranda balcony, and a well-shaded pool deck provide guests plenty of room to spread out and enjoy island living. The views are breathtaking.

This grand estate is not only one of the largest rental villas on the entire island, but it also is a notable landmark. Virtually anyone on the island will be familiar with the Castle in the East End. 

While we are neighbors to the Wreck of the 10 Sails Park and the police constable's residence to the north, this property enjoys no residential neighbors to the north or south for 500 feet in either direction.  This is a gated and walled estate with a private beachfront. 

The owner takes immaculate care of the home, making upgrades each fall to keep the experience not only refreshing and pleasant for repeat guests, but for newcomers to Cayman as well.  

Sleeping Arrangements
(Sleeps 14 guests total, 11 adults max)

  • Primary Suite – spans entire third-floor, ocean views, king bed, private balcony, television, small dining nook, ensuite with shower.
  • South Suite – second-floor, ocean views, king bed, small workstation, ensuite with shower.
  • Family Suite – second-floor, king bed + bunk beds, ensuite with shower.
  • Pool Suite – lower level, queen bed, ocean views, private entry, walk-out access to the pool deck, television, ensuite with shower.
  • Bunk Suite – lower-level, full-over-full bunk beds, television with Apple TV, ensuite with shower.
  • 2 folding cribs are stored in the Bunk Suite closet.

Cayman Castle’s Unique Features 


  • A gorgeous, oceanfront infinity pool heated to 84 degrees in winter months free of charge (Dec 15 - Apr 15).
  • Spacious pool veranda furnished with an outdoor sectional sofa, chaise sun lounges, and a dining table with seating for 8.
  • Upper and lower oceanfront terraces furnished with Adirondack chairs and chaise sun lounges.
  • Large Beach Cabana and 4 kayaks (2 tandem and 2 singles) provided complimentary on the villa's private beach.
  • Walking distance to Ocean Frontiers dive shop and dining options (Eagle Rays and Big Tree BBQ) makes this a convenient option for families; Tukka Restaurant nearby provides complimentary shuttle service for Castle guests and the Italian Kitchen will deliver. 
  • A custom-made 17-foot mosaic dining table on the veranda balcony seats 18 guests with panoramic ocean views while you dine.
  • Propane grilling station with granite countertops located between the main villa and guesthouse.
  • Private gated driveway with plenty of off-street parking. 


  • The kitchen, dining, and living areas are all oceanfront on the second-floor providing panoramic views throughout.
  • The modern kitchen features a GE oven, Bosch dishwasher, 48" SubZero refrigerator, ceramic glass stovetop, microwave, Keurig and drip coffeemakers, mixer, blender, and breakfast bar seating for 8.
  • Cozy living area with a 60" flatscreen TV and full channel programming for unwinding after a day of sun and surf.
  • High-speed wifi with mesh network for the pool and balcony areas.
  • L-shaped bar with a beverage fridge just off the pool deck on the lower level.
  • Back-up, full-sized fridge with ice maker in the laundry room.

For larger groups, Cayman Castle can also be rented with the optional 2 bedroom guesthouse next door which sleeps an additional 6 guests, 5 adults max. The guesthouse is equipped with its own pool, separate driveway, and full kitchen.

*Note: A Cleaning Fee is added due to enhanced cleaning and sanitation.

**Additional tandem kayaks are available for discounted rental.  A signed waiver is required. 

Show more details ...


Private Infinity Pool
Pool Heat (Free in Winter)
Snorkeling Reef
2 Tandem Kayaks Provided
2 Single Kayaks Provided
Gated Driveway
Central A/C
High-speed Fiber Internet
Keyless Entry
Flat Screen TVs
Satellite TV
Apple TV (3)
Bluetooth Speakers
Beach Cabana
Gourmet Kitchen
Modern Appliances
Keurig & Drip Coffee Makers
Propane Grill
Ice Coolers
Hair Dryers
Linens Provided
Beach & Bath Towels Provided
No Pets Permitted
No Smoking Allowed
Off-Street Parking
Additional Kayaks for Rent

Beach Notes

Cayman Castle sits on a 2 acre gated estate in "Gun Bay" in East End.  Adjacent to 6 acres of government land that includes the "Wreck of the 10 Sails" park and the East End Constable's office, Cayman Castle has virtually no neighbors within well over 500 feet.  2-3 lunch places are within walking distance and Tukka Restaurant is only a mile north.

Further north are 2 large resorts (Morritts and The Reef) where they maintain manicured beaches, pools, restaurants, bars and watersports.  These resorts are great places to entertain older kids and are open to the public for the day.

The beach at the Castle is white sand and quite private.  We have three thatched cabanas, 4 kayaks, and 6 lounge chaises on the beach.  Most guests will spend the day sunning around the pool, but we provide the beach option too.  The water is more snorkeling than swimming here...it is a marine environment and we recommend pool shoes or fins for foot protection.  We have a great snorkeling site straight out 200 yds from the Castle marked with a white PVC pole.  You may tie up the kayaks to this pole as well. 

General Grand Cayman Beach Notes

All beaches in Grand Cayman are technically “public” since the Queen owns up to the high water mark and the shoreline quality behind your property may vary seasonally. Be advised that the beach or water entry behind your property may vary slightly from the images on our website because of the weather. The next-door beach is also always available for your use.

Ocean Debris & Sargassum Seaweed

Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. 

Should sargassum weed be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.

Beaches that either face west or are protected by coves/barriers tend to be much less affected by any flotsam or seaweed. 

 Your Concierge & Service Fee includes your Guest Services Membership.

Member Benefits

  • Centralized on-island Guest Services & Welcome Center
  • Unlimited use of Private Fitness Center (18+ yrs.)
  • Business Center Access: computers, printer, scanner, & Fedex/DHL supplies
  • Proprietary Guest benefit & discount card for 10% Discounts at Local Businesses & Restaurants
  • Discounted Private Coach Transport To/From Restaurants
  • 10% advance booking discount for private charter
  • Complimentary use of snorkel equipment
  • Guest parcel receipt & hold for check-in
  • Jacques Scott Wine & Spirits pre-order & hold for check-in
  • Referral to preferred vendors, guest services desk assistance
  • Airport arrival Fast-Track VIP Process (fee charged by CAA)
  • Special event/dinner reservations

At-Villa Benefits

  • Welcome amenity basket
  • Complimentary early check-in, if no check out on same day
  • Day-after-arrival guest services follow-up
  • Gilchrist & Soames bath products
  • Pre-stocking of groceries & beverages (delivery fee applies)
  • Arrange chefs, cooks, babysitting & family photography
  • $3,000 of Accidental Villa Damage Protection
  • Complimentary pack-n-plays, booster seats, & baby gates
  • Tandem kayaks available for discounted rental*

*Signed waiver required.

Guest Reviews of Cayman Castle

442 Austin Connally Drive Grand Cayman , KY

5 out of 5 stars based on 23 user reviews

Picture Perfect ❤️

Review by Kristen on 07/11/2024
5 out of 5
This property is spectacular. It had plenty of space for 15 adults and 5 older kids. We never felt cramped and had plenty of space for playing cards, eating meals, pool time, and hanging out. We survived our first hurricane in this house! This house is SOLID. The owners have taken great care of the property and the attention to detail with furnishings is top notch. Highly recommend!!

My family loved our week staying at this property

Review by Carol on 06/10/2024
5 out of 5
My family of 14, including me, a senior citizen, my middle-age children and my 20 something grandchildren enjoyed a week staying in this property. It was an easy 40 minute drive from the airport. Right on the ocean with an infinity pool. Well furnished with comfortable beds and spacious bathrooms. There were several good restaurants within walking distance we only needed one or two contact with the property managers. They were very responsive and handled the minor problems quickly. I would highly recommend this property to anyone looking for a unique experience.


Review by Joy on 03/19/2024
5 out of 5
The Cayman Castle was outstanding! We were a large group and had plenty of room to spread out and have privacy if wanted. The great room, kitchen and outside patio area were very big and we did not feel crowded at all when all together. The views were fantastic and the facility extremely clean. My only thought for anyone that wants to spend time at 7 mile beach and Georgetown restaurants (I didn\'t) is that it is a bit of a drive, but for me I loved the fact it was in a quiet area without the crowds of the populated side of the island. There were a few restaurants close to the castle that were great! We took advantage of having the house pre-stocked with groceries and also used one of their recommended chefs one night. Check in and any contact we had with the management company was seamless. We will be back!

Awesome Property!

Review by Cayman Crew 2024 on 02/26/2024
5 out of 5
We had a beautiful time at the Cayman Castle and Guesthouse. Property was exactly as advertised. Clean and well maintained. Cayman Villas staff did a superb job in attending to our requests and needs. Very enjoyable stay and we plan to do it again at the Castle! Love East End Grand Cayman.  

Beautiful home and location

Review by Sue on 02/12/2024
5 out of 5
Our family really enjoyed our stay at the castle! We had 8 adults and 2 kids-plenty of space for everyone. We especially enjoyed the shady, comfortable area around the pool and the gorgeous views. We also loved the beach with the shady wooden palapa and chairs. The snorkeling was good especially around the buoy nearest to the house. We would definitely recommend this home to anyone!

Better Than Advertised!

Review by Lesa on 01/13/2024
5 out of 5
Our group had 15 people ranging in age from 5 months to 75 years old. The property is even better than advertised. We never felt cramped or lacked for any room. The Castle and guest house are wonderfully stocked with lot of towels and any kitchen gadget you would need. Lots of books, games, puzzles, pool toys and kayaks. A wonderful place to spend our anniversary with 4 generations of our family. We would love to come back some day.

Beautiful Island

Review by The Chester Family on 12/06/2023
5 out of 5
Beautiful island. Beautiful people. Wonderful place for family. Reunion-vacay! 

40th Birthday!

Review by Iowa Friends on 12/06/2023
5 out of 5
Partied like rockstars for my 40th!! Starfish point is great. Tukka has excellent food. Snorkeling at Rum Point(big coral perpendicular to dock). Don't miss Stingray City!

Absolutely Spectacular!

Review by The Donovans on 12/06/2023
5 out of 5
Absolutely spectacular! We loved every moment spent in this hidden gem. Until next time...

Enjoyed Our Stay Immensely

Review by The Smiths on 12/06/2023
5 out of 5
We have enjoyed our stay immensely. The views from the veranda are beyond compare. The private beach is made for total relaxation and book reading. There is nothing we can think of that would have made it better. Many eateries very close that were great. We highly recommend the Italian Kitchen, La Casita, and The Czech Inn Grill(fantastic burgers). Owner is very entertaining!

Very Lovely Spot

Review by The Stricklands on 12/06/2023
5 out of 5
The house is in a very lovely spot. The ocean views are amazing, even the stars are spectacular at night. The sun shining in the window in the morning letting us know it\'s time to awake to another wonderful day on the island. We enjoyed pizza from the Italian Kitchen. It is delicious. La Casita was also wonderful for dinner. Over The Edge- fried chicken- best on the island. Sorry to leave the island but we will be back again. Leaving with fond memories.

Cayman Castle

Review by Michael on 07/02/2023
5 out of 5
Awesome place great views. Great time. Loved eastern side of the island. Better than pictures.


Review by Ramona on 04/03/2023
5 out of 5
Exceeded expectations! Excellent location. Quiet east end of island. Snorkeling by the barrier reef was some of the best on the island. Several restaurants & bars within walking distance. House was perfect for our group of 18 spanning 3 generations. We loved the Cayman Castle!

Best Friends Trip to Paradise

Review by Ronnie on 12/20/2018
5 out of 5
We booked this trip 6 months in advance and every day till we left for our trip we kept looking at pictures of the castle. It did not disappoint us the castle is absolutely beautiful. We had 13 of us for our trip 8 adults and 5 teenagers. So the 5 bedroom house plus the guest house with 2 bedrooms was the perfect accommodations. I planned things out very well ahead of time had the house stocked with food before we arrived which made things so much easier. Just show up and the vacation started. All of us jumped right into the water of the back of the house and swam out to the coral reef which is only about 500 yards out. It is one of the best dive spots on the island. Each morning we either swam out to that spot or took one of the kayakes which there are four out to the coral reef. The house is everything it looks like in the pictures. The pool off the deck is amazing and we spent so much of our time just in that pool no one ever wanted to leave the house. The chairs that are placed on the two lower decks is where we spent every night. The location for the house is wonderful a very quite part of the island with some great restaurants very close by. The dive shop which is Ocean Frontiers is very close we walked to it each day. They had a great staff and we all went on many dives together as a group. This was a wonderful trip for all of us and we do hope to go back next year. All everyone kept saying the entire week is it does not get better than this. The house is not just on the beach it is out in the ocean. The Cayman Castle is a wonderful place to take family or friends on an amazing vacation.

Fit for a King & Queen

Review by Woody on 12/20/2018
5 out of 5
Every other year we take a "family" vacation..large group of 19. Ages ranging from 65-1. After much research The Castle was just what I was looking for..plenty of room & privacy. And let's not forget BEAUTIFUL. We were over the guest limit so I rented a 2 BR condo at the nearby (about 2 miles) Reef Resort for overflow. Worked out great for nephews with young children. The house is stunning & the view is breathtaking. All the modern amenities one would expect. Having private LARGE baths per BD was a major plus. The balconies overlooking the water are wonderful & the pool sitting area is huge with the convenience of "walk into the sea" stairs on lower walking path. A VERY LARGE mahogany/ceramic inlaid table on the second level balcony was used constantly, plenty of room for everyone!! The guest house was in itself a dream retreat!!!! And the grounds are meticulously kept and GORGEOUS. Flowers & lush tropical plants everywhere!! Comp Kayaks were used every day & the kids loved it. Dive shop is a "shells throw" away. Only semi-negatives: AC controls are locked in at 73*..this may sound comfortable temp but it got somewhat warm in upper master and ground floor (oddly during the night for sleeping?) I know the cost of electricity is absurd & they have to control usage, but would have preferred a little cooler. The guest house stayed very cold. The beach is not the greatest at this site..being on the east end of the island this is the first land where debris drifts onshore.. And seaweed..the water is not slick calm & has patchy grass bottom. We never swam here & opted to go down the road a ways to RUM POINT!!! PICTURE PERFECT WATERS!! A NOT TO MISS AREA! IDEAL SNORKELING!!! Being on the East end the location is removed from the hub of Georgetown (45 minute drive) RUM POINT is about 20 minutes away & very very nice.

Great Family Vacation

Review by Gigi on 12/20/2018
5 out of 5
Our family stayed at Cayman Castle (and guest house) for 2 weeks in June and were very pleased with the accommodations. The house is large enough to accommodate multiple families, view is beautiful, pool area works well with both sun and shade, diving convenient, (practically next door), kayaks for snorkeling a nice extra, loved the 2 large washers and dryers! Only negative was the lengthy drive to 7 mile beach and Georgetown but it\'s hard to have everything!

Perfect Getaway for Large Family or Group of Friends

Review by Bryan on 08/03/2016
5 out of 5
From start to finish this vacation couldn't have been more seamless. Everyone at Grand Cayman Villas was super helpful months prior to our arrival in ensuring we were set up with everything we needed from car rentals to groceries arriving at the house before we got there. They have a very user friendly app that gives you access to literally every little thing you will need while vacationing and lets you do what you are actually there for...RELAXATION! Beautiful house, amazing service and a definite MUST if you are vacationing in Grand Cayman!

Wonderful family vacation

Review by John on 07/16/2016
5 out of 5
This is our second trip to Cayman Castle. We take the family to the Caribbean every other year. The grandkids age one to fifteen requested we return to Cayman Castle. This is our sixth trip and the first time there was a request to go back to the same place.!

Amazing and Enchanting

Review by Laura on 07/07/2016
5 out of 5
Cayman Castle is an excellent home! We were extremely happy with the property. The amenities were amazing with high-end furnishings, great linens, plenty of beach towels, and everything we could want! The kitchen is nicely equipped - there wasn't anything we felt we needed during our stay. The booking process with Grand Cayman Villas was no fuss. Any questions we had were answered right away. We never wanted to leave the Castle because it was so enchanting. We did go to Rum Point beach a few times to enjoy the wonderful water and cocktails.

Simply Phenominal

Review by Garrett on 06/04/2016
5 out of 5
Our stay in the caymans castle and guesthouse was simply phenomenal. everything is even better than the pictures. the house has everything that you need or could want. from a FULLY stocked kitchen to additional supplies...you'll want for nothing. our chef found everything in great order and great supply. the infinity edge pool is great for lounging and taking in the scenery as well as the multiple patios. with 12 adults we never felt like we were on top of each other because the property is incredibly spacious. we did not want to leave and are already planning our return. the entire process from reservation to check-in was incredibly smooth. guests are strongly encouraged to rent a vehicle. There's a mini grocery store about 10 minutes away as well as a liquor store. In addition, we discovered the Italian kitchen which opens at 5 daily and will deliver to the castle. we are fortunate and blessed to have stayed in the castle. special thanks to the entire Grand Cayman Villa team.

What a wonderful week

Review by Graham on 02/20/2016
5 out of 5
After a week of debating between hotels or homes and which side of the island we chose to stay at the Cayman castle. We were concerned about not staying on the tourist side of the island, and difference in beaches but after spending time on both sides we were very pleased with our decision. 3 decks/balconies, pool, gorgeous sitting area in shade by pool we had quite the relaxing time on property, never wanted for anything. I was beyond impressed with the professionalism and thoroughness of the management company. Between the app and staff I had all the information to be prepared for my trip. While there were only two of us, there was plenty of room for 5 couples or children. Home is gorgeous with the right balance of island décor and modern amenities. Restaurants and areas of interest were more enjoyable on this side of the island, we prefer to understand the charm of an island over visiting a Margaritaville. Will be going back again and probably bring a few other friends. Highly recommend for a vacation or special event

Highly Recommend!

Review by Road Crew on 10/10/2015
5 out of 5
Our trip to the Cayman Castle was incredible. If you value your privacy and space, I don't think you will find a better place on the island. My wife and I, plus our 5 kids aged 9-16, plus my parents in their early 70's stayed at the Castle for one week. There was plenty of space for all of us, and none of us wanted to leave at the end! There are so many areas to enjoy on the property it was almost hard to find time to enjoy them all within a week. The kitchen is large and very nice to cook in. We found it much more convenient to prepare our own meals than to eat out. We didn't want to leave the house! The house sits on a point and has more than 180 degree views that never get old. The rooms were very comfortable and the house was well decorated.The property's kayaks were also a huge hit - we used them every day to explore the ocean in front of the house. If you are ambitious, there are some amazing snorkel spots that are a ways out.We also enjoyed the incredible close proximity of the Ocean Frontiers Dive Shop. We booked snorkeling and diving trips with them, as well as a trip to Sting Ray City. The dive shop is top notch!We started our trip at the Ritz Carlton on 7 mile beach for one night, then spent a week at the Castle, then spent one more night on 7 mile beach at the Marriott. We found it interesting to compare the hotel style vacation on 7 mile beach with the private home style vacation on the east end. And while the hotels were very nice, they did not compare in any way to our stay at the castle. We want to go back and do it all over again! It was a perfect vacation.

House, property and location were phenomenal!

Review by Bob H on 08/15/2015
5 out of 5
We had a great time. The house was unique and suited our needs. It was in excellent condition and everything worked well. We had no issues. The booking was easy and understandable. The directions and operations of the house were clear and precise. We didn’t need the on-island manager, so no feedback there. I have no recommendations on improvement, just keep up the good work. If I had a property in the area, I would hire your to manage and promote it.
Begins Ends Daily
Jan 01, 1970Jan 01, 1970 $1,295
May 25, 2024Aug 14, 2024 $1,650
Aug 15, 2024Nov 01, 2024 $1,250
Nov 02, 2024Nov 22, 2024 $1,650
Nov 23, 2024Nov 30, 2024 $1,950
Dec 01, 2024Dec 18, 2024 $1,750
Dec 19, 2024Dec 26, 2024 $3,450
Dec 27, 2024Jan 03, 2025 $3,750
Jan 04, 2025Mar 01, 2025 $1,950
Mar 02, 2025Apr 12, 2025 $2,150
Apr 13, 2025May 24, 2025 $1,500
May 25, 2025Aug 14, 2025 $1,650
Aug 15, 2025Nov 01, 2025 $1,250
Nov 02, 2025Nov 22, 2025 $1,650
Nov 23, 2025Nov 30, 2025 $1,950
Dec 01, 2025Dec 18, 2025 $1,750
Dec 19, 2025Dec 26, 2025 $3,450
Dec 27, 2025Jan 03, 2026 $3,750
Jan 04, 2026Feb 28, 2026 $1,950
Mar 01, 2026Apr 11, 2026 $2,150
Apr 12, 2026May 23, 2026 $1,500
May 24, 2026Aug 13, 2026 $1,650
Aug 14, 2026Oct 31, 2026 $1,250
Nov 01, 2026Nov 21, 2026 $1,650
Nov 22, 2026Nov 29, 2026 $1,950
Nov 30, 2026Dec 17, 2026 $1,750
Dec 18, 2026Dec 25, 2026 $3,450

Taxes & Fees

  • 13% Occupancy Tax added to all rates.
  • 12.90% Villa Concierge & Service Fee added to all rates.
  • A Departure Cleaning Fee is required for all stays.
  • A refundable damage deposit is required for all stays.
  • Refundable damage deposits will be returned to the guest 7 days after departure pending any damages.
  • We accept Visa, MC, Discover, and Bank Wire for payments. 

Booking Rules

  • 5 nights minimum stay required.
  • 6 nights minimum and full occupancy required over Thanksgiving week.
  • 7 nights minimum and full occupancy required over Christmas and New Year's week.
  • Christmas & New Year's are split into two rental periods. Please inquire directly with your travel dates prior to booking.
  • Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking.
  • Extended stays unlock additional discounts. Inquire for promo code.
  • Must be 25 years or older to book and must occupy the property during the entire stay.

Villa Cleaning & Sanitation

All villas are cleaned and sanitized prior to each guest's arrival. We also ask our owners to provide a starter supply of extra cleaning products.

Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival.

Map Notes

Nearby Points of Interest

Getting Around

A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island

For rental cars, we recommend Budget CaymanAvis, or Marshalls.

Inquire About This Villa:

Comments & Questions*
* Required fields
Book Your Stay

Have questions about this property? Email us using the white button below.